[go: up one dir, main page]

US10301489B2 - Comb polyurethane dispersants - Google Patents

Comb polyurethane dispersants Download PDF

Info

Publication number
US10301489B2
US10301489B2 US15/518,520 US201515518520A US10301489B2 US 10301489 B2 US10301489 B2 US 10301489B2 US 201515518520 A US201515518520 A US 201515518520A US 10301489 B2 US10301489 B2 US 10301489B2
Authority
US
United States
Prior art keywords
pigments
sum
polyurethane
dispersant
diisocyanate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
US15/518,520
Other languages
English (en)
Other versions
US20170240756A1 (en
Inventor
Howard P. Klein
Frank Bertens
Petra Vanderstraeten
Jolande Celis
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Huntsman Petrochemical LLC
Original Assignee
Huntsman Petrochemical LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Huntsman Petrochemical LLC filed Critical Huntsman Petrochemical LLC
Priority to US15/518,520 priority Critical patent/US10301489B2/en
Assigned to HUNTSMAN PETROCHEMICAL LLC reassignment HUNTSMAN PETROCHEMICAL LLC ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BERTENS, Frank, CELIS, Jolande, VANDERSTRAETEN, Petra, KLEIN, HOWARD P
Publication of US20170240756A1 publication Critical patent/US20170240756A1/en
Application granted granted Critical
Publication of US10301489B2 publication Critical patent/US10301489B2/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
    • C08G18/3823—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups
    • C08G18/3825—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups containing amide groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
    • C08G18/5036—Polyethers having heteroatoms other than oxygen having nitrogen containing -N-C=O groups
    • C08G18/5039—Polyethers having heteroatoms other than oxygen having nitrogen containing -N-C=O groups containing amide groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/08—Polyurethanes from polyethers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/45—Anti-settling agents

Definitions

  • Embodiments described herein are generally related to non-aqueous and aqueous inks and pigmented coatings, and more specifically, to a comb polyurethane dispersant for inks and pigmented coatings.
  • an ink composition is prepared by mixing the concentrated pigment dispersion which contains pigment, water, dispersant and the like with water, resin, a water-soluble organic medium, and other ingredients.
  • the pigment dispersion is generally stabilized by a dispersant which serves to prevent the pigment particles from agglomerating and settling out of the carrier. While prior ink compositions showed acceptable stability for the pigment dispersion, improved pigment dispersion is still needed to further lower the ink viscosity, impart better print density, increase pigment loading, and lower milling times for ink and coating systems.
  • Embodiments described herein provide a dispersant for ink and pigmented coatings.
  • An exemplary dispersant is a polyurethane including oxamide diol groups.
  • Use of dispersants as taught herein enables the preparation of a wide variety of inks and coatings having high pigment loading and existing within a conventionally-useful viscosity range.
  • the dispersant includes a polyurethane having oxamide diol groups.
  • the dispersant includes a polyurethane formed by reacting a diisocyanate and an oxamide diol.
  • a composition in another embodiment, includes a pigment component, a dispersant including a polyurethane having oxamide diol groups.
  • weight average molecular weight is given by:
  • M w ⁇ i ⁇ n i ⁇ M i 2 ⁇ i ⁇ n i ⁇ M i
  • ni is the number fraction of molecules of molecular weight Mi.
  • Mw is typically determined by Gel Permeation Chromatography (GPC).
  • Embodiments described herein provide a dispersant for ink and pigmented coatings.
  • the dispersant is a comb polyurethane.
  • An exemplary comb polyurethane is a polyurethane including oxamide diol groups.
  • a component of a liquid ink composition or a pigmented coating composition according to embodiments described herein is a comb polyurethane, made in accordance herewith, which serves to stabilize the pigment against agglomeration in the formulation.
  • a comb polyurethane suitable for use in an ink composition or a pigmented coating composition is formed by reacting an oxamide diol with a diisocyanate.
  • the product resulting from such a reaction may be a polyurethane having oxamide diol groups.
  • the diisocyanate used for forming the polyurethane comb polymer may be any suitable diisocyanate.
  • the diisocyanate may be aromatic, aliphatic, or cycloaliphatic.
  • an aromatic diisocyanate such as methylene diphenyl diisocyanate (MDI), or modified MDI such as hydrogenated MDI, is used.
  • aromatic diisocyanates include p-phenylene diisocyanate, polymethylene polyphenylisocyanate, 2, 6-toluene diisocyanate, dianisidine diisocyanate, bitolylene diisocyanate, naphthalene 1,4-diisocyanate, bis(4-isocyanatophenyl)methane, bis(3-methyl-4-isocyanatophenypmethane, and 4,4′-diphenylpropane diisocyanate.
  • Suitable aliphatic diisocyanates include hexamethylene diisocyanate (HDI), alkylene diisocyanate with 4 to 12 carbon atoms in the alkylene radical, such as 1, 12-dodecane diisocyanate or 1,4-tetramethylene diisocyanate, and bi-functional monomer of tetraalkyl xylene diisocyanate, such as tetramethyl xylene diisocyanate.
  • HDI hexamethylene diisocyanate
  • alkylene diisocyanate with 4 to 12 carbon atoms in the alkylene radical such as 1, 12-dodecane diisocyanate or 1,4-tetramethylene diisocyanate
  • bi-functional monomer of tetraalkyl xylene diisocyanate such as tetramethyl xylene diisocyanate.
  • Suitable cycloaliphatic diisocyanates include 1,3 and 1,4-cyclohexane diisocyanate as well as any mixture of these isomers, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethyl-cyclohexane (isophorone diisocyanate) as well as its isomers, 4,4′-2,2′- and 2,4′-dicyclohexylmethane diisocyanate as well as the corresponding isomer mixtures.
  • the comb polyurethane is formed by reacting oxamide diol with a diisocyanate as shown below:
  • R′ may be any suitable aromatic, aliphatic, or cycloaliphatic group.
  • R′ is a biphenyl group and the diisocyanate is MDI.
  • the product comb polyurethane has the following structure:
  • the terminal group may be the oxamide diol group, as shown above, or may be a hydroxide group.
  • the comb polyurethane is formed by reacting oxamide diol with MDI as shown below:
  • the product comb polyurethane has the following structure:
  • the comb polyurethane from reacting oxamide diol and a diisocyanate has an average molecular weight ranging from about 13,000 to about 40,000, depending on the ratio of oxamide diol to the diisocyanate, and has neutral anchoring groups.
  • a conventional polymer dispersant may have an average molecular weight of around 5,000 and have basic anchoring groups.
  • the comb polyurethane is very stable and highly effective in reducing the dispersion viscosity resulting in higher pigment loading and in reduced milling times for ink and coating compositions.
  • the comb polyurethane may be soluble in water or in non-polar solvents.
  • the comb polyurethane may have a backbone that is hydrophilic and pendant groups that are hydrophobic. Alternatively, the backbone is hydrophobic and the pendant groups are hydrophilic.
  • the pendant group of the comb polyurethane may be oxamide, as shown above.
  • the oxamide diol may be synthesized by first forming a reactive six-member lactone, and then reacting the six-member lactone with a monofunctional, amine-terminated polyether, or a mono-polyetheramine.
  • the six member lactone may be synthesized by condensation of a difunctional amino alcohol with diethyl oxalate as shown below:
  • R2 is a hydrogen atom or an alkyl group having one to eight carbons.
  • the difunctional amino alcohol is diethanolamine (DEA) and the six member lactone is 4-hydroxyethyl-2,3-morpholinedione (HEMD), and the reaction is shown below:
  • the six member lactone is then reacted with a mono-polyetheramine, such as Huntsman's SURFONAMINES amines, to form the oxamide diol.
  • a mono-polyetheramine such as Huntsman's SURFONAMINES amines
  • HEMD is reacted with the mono-polyetheramine to form oxamide diol, as shown below:
  • R is prepared by addition of ethylene oxide (EO) and/or propylene oxide (PO) with an alcohol having various amount of carbon atoms.
  • EO ethylene oxide
  • PO propylene oxide
  • a PO block is added at the end of the molecule bearing the amine group.
  • R may have the following structure:
  • y may be 5% to 95% of the sum of y and z
  • z may be 5% to 95% of the sum of y and z.
  • the conversion of the HEMD and amine to the oxamide diol may be at least 90%, such as from about 90% to about 95%.
  • the comb polyurethane component of the ink composition or the pigmented coating composition according to embodiments described herein may be provided in any amount between about 0.5% and about 25% by weight, such as between about 1% and about 10% by weight, based on the total weight of all pigment present in the ink composition or pigmented coating composition.
  • the pigment component may be an insoluble colorant material, such as phthalocyanine.
  • an insoluble colorant material such as phthalocyanine.
  • organic and/or inorganic pigments may be present in an ink composition or a pigmented coating composition.
  • inorganic pigments are carbon black, titanium oxides, chromates, sulfides, and iron oxides.
  • organic pigments are azo pigments (such as azo lakes, insoluble azo pigment, condensed azo pigments, chelate azo pigments, monoazo pigments, including monoarylide, B-naphthol, naphthol AS, benzimidazolone, and metal precipitated azo, as well as disazo pigments, including diarylide, disazo condensation, diazopyrazoione, and bisacetoacetarylide), polycyclic pigments (such as phthalocyanine pigments, perylenes, perylene, and perinone pigments, anthraquinone pigments, quinacridone pigments, dioxazine pigments, thioindigo pigments, isoindolinone pigments, and quinophthalone pigments), lake pigments (such as base dye lakes, and acid dye lakes), nitro pigments, nitroso pigments, and aniline black daylight fluorescent pigments.
  • azo pigments such as azo lakes, insoluble azo pigment, condensed azo
  • pigments include isoindoline, isoindolinon, indigoid, diketopyrrolopyrrole, triarylcarbonium, metal complexes, pearl, liquid crystal pigments, fluorescence, and functional derivatives of the above-mentioned pigments. Additionally, suitable pigments include those that are dispersed in a water phase or those whose surfaces have been treated with a surfactant or a polymeric dispersing agent (such as graphite carbon).
  • the amount of pigments present in an ink composition or pigmented coating composition may vary and may be present in any amount ranging from about 1% to about 50%, alternatively from about 1% to about 40%, and in another embodiment, from about 2% to about 10% by weight, based on the total weight of ink or pigmented coating composition.
  • the ink composition or pigmented coating composition may include a solvent, which is sometimes referred to as the carrier medium.
  • the carrier medium can be either aqueous or non-aqueous.
  • the carrier medium may be water or may comprise a mixture of water and at least one organic solvent which is soluble in water.
  • Exemplary water-soluble organic solvents include one or more polyhydric alcohols. Suitable polyhydric alcohols include ethylene glycol, propylene glycol, and diols such as butanediol, pentanediol.
  • Glycols and glycol esters are also useful, and include those such as glycerol, propylene glycol laurate; polyalkyl glycols such as polyethylene glycol; and lower alkyl ethers of polyhydric alcohols, such as ethylene glycol monomethyl ether, ethylene glycol mono-ethyl ether and ethylene glycol mono-butyl ether.
  • Suitable water-soluble organic solvents include lower alcohols and all their isomers having fewer than about eight carbon atoms per molecule such as methanol, ethanol, propanol, iso-propanol; ketones such as acetone; ethers such as dioxane; esters such as ethyl acetate, propyl acetate, and lactams such as 2-pyrrolidone.
  • Still further suitable solvents include aliphatics such as hexane and mineral spirits; aromatics such as toluene; triglycerides such as soy bean oil and castor oil; and fatty acids such as tall oil fatty acids.
  • the amount of solvent present in the ink composition or the pigmented coating composition may be any amount in the range of between about 10% to about 60%, such as from about 40% to about 55% based on total weight of the ink composition or the pigmented coating composition.
  • Pigments may be incorporated into a pigmented coating composition by mixing a pigment dispersion and a grind resin.
  • the pigment dispersion may be a mixture of a pigment and a dispersant.
  • Suitable grind resins typically include the polymerized residue of the styrene and/or substituted-styrene monomer and a carboxylated monomer.
  • the carboxylated monomer is selected from the group consisting of substituted or unsubstituted acrylic acid, methacrylic acid, maleic acid, half esters of maleic acid, citriconic acid, itaconic acid, and combinations thereof.
  • the grind resin and the pigment dispersion are the same. In this instance, an additional amount of pigment dispersion acts as a grind resin.
  • the pigment dispersion and the grind resin may be mixed using mills such as a ball mill, grind mill, continuous mill, or by any other means that effectively integrates the pigment dispersion into the grind resin.
  • the pigmented dispersion and grind resin are effectively integrated when the desired particle size of the pigment is achieved, the pigment is appropriately wetted by the grinding resin, and the pigment is uniformly dispersed throughout the grind resin.
  • the grind resin is present in an amount from about 0.1% to about 40% by weight based on the pigment. In an alternative embodiment, the grind resin is present in an amount from about 1% to about 30% by weight based on the pigment. In a still further embodiment, the grind resin is present in an amount from about 2% to about 20% by weight based on the pigment. In an embodiment, the size of the pigment is less than or equal to about 1 micron after grinding, as measured by ultrasound technology using DT-1200, which is manufactured by Dispersion Technologies Company.
  • An ink or coating composition may be suitably prepared by combining the various components and mixing them in a blender to homogenize, and grinding them in a bead mill.
  • the blender may be an ordinary kitchen blender.
  • a surfactant may be added to wet the pigment and modify the surface tension of the ink to control penetration of the ink into the paper.
  • suitable surfactants include nonionic, amphoteric, anionic, zwitterionic, and cationic surfactants, and those of ordinary skill in this art are aware of the surfactants employed in this field.
  • additives such as binders (resins), biocides, humectants, chelating agents, viscosity modifiers, and defoamers may also be present in an ink composition according to embodiments described herein.
  • binders resins
  • biocides biocides
  • humectants chelating agents
  • viscosity modifiers and defoamers
  • acrylic and non-acrylic polymers may be added to improve properties such as water fastness and smear resistance.
  • acrylic and non-acrylic polymers may be added to improve properties such as water fastness and smear resistance.
  • the comb polyurethane may also act as a dispersant which may be used to prepare a pigment concentrate.
  • the pigment concentrate may be utilized to prepare ink compositions and pigmented coatings.
  • the pigment concentrate may include a pigment, a solvent, one or more additives (defoamer, wetting agent), and the comb polyurethane.
  • a grind resin may be included in the pigment concentrate.
  • the amount of solvent in the pigment concentrate may range from about 20 to 70% by weight.
  • the amount of the comb polyurethane acting as a dispersant in the pigment concentrate may range from about 5 to about 80% by weight.
  • the amount of the comb polyurethane acting as a dispersant may be the active amount of dispersant based on the total amount of the pigment used, and may be expressed as a weight percentage. For example, 5 g of the comb polyurethane is added to a pigment concentration including 18 g of pigment, and the active amount of dispersant is 27.8% (5/18).
  • HEMD granules were added to a 250 ml flask.
  • the flask was fitted with an overhead stirrer, thermometer probe, nitrogen inlet and condenser.
  • SURFONAMINE® L207 (heated to 50 degrees C. in an oven) was added to the flask.
  • the mixture was stirred and heated under nitrogen.
  • HEMD was completely dissolved and set temperature was increased.
  • the mixture was kept at this temperature for about 2 hours and stirred under nitrogen.
  • the product was cooled to room temperature.
  • the final product, oxamide diol is a clear colorless liquid at room temperature.
  • Each batch of the oxamide diol was added to a 250 ml flask.
  • the flask was fitted with an overhead stirrer, thermometer probe, nitrogen inlet and condenser.
  • the diol was heated to 80 to 90 degrees Celsius.
  • an amount of SUPRASEC® 1306 (heated to 50 degrees C.), based on the abovementioned ratio, was added to the flask.
  • the mixture was stirred and heated under nitrogen. When the mixture reached 110 degrees C., the mixture was kept at this temperature for about 2 hours and stirred under nitrogen.
  • the product, comb polyurethane was cooled to room temperature.
  • the comb polyurethane dispersants are clear yellow liquids at room temperature.
  • Table 5 shows the compounds used for preparation of comb polyurethane dispersants:

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Paints Or Removers (AREA)
US15/518,520 2014-11-14 2015-11-05 Comb polyurethane dispersants Active US10301489B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US15/518,520 US10301489B2 (en) 2014-11-14 2015-11-05 Comb polyurethane dispersants

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201462079660P 2014-11-14 2014-11-14
PCT/US2015/059236 WO2016077147A1 (en) 2014-11-14 2015-11-05 Comb polyurethane dispersants
US15/518,520 US10301489B2 (en) 2014-11-14 2015-11-05 Comb polyurethane dispersants

Publications (2)

Publication Number Publication Date
US20170240756A1 US20170240756A1 (en) 2017-08-24
US10301489B2 true US10301489B2 (en) 2019-05-28

Family

ID=55954878

Family Applications (1)

Application Number Title Priority Date Filing Date
US15/518,520 Active US10301489B2 (en) 2014-11-14 2015-11-05 Comb polyurethane dispersants

Country Status (8)

Country Link
US (1) US10301489B2 (ja)
EP (1) EP3218423B1 (ja)
JP (1) JP6603714B2 (ja)
KR (1) KR102465005B1 (ja)
CN (1) CN107075106B (ja)
BR (1) BR112017008202B1 (ja)
MX (1) MX391841B (ja)
WO (1) WO2016077147A1 (ja)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10106639B2 (en) * 2016-09-16 2018-10-23 Riso Kagaku Corporation Oil-based inkjet ink
US10793667B2 (en) 2019-02-07 2020-10-06 Covestro Deutschland Ag Curable compositions, products and articles formed therefrom, and methods of forming the same
CN112778485A (zh) * 2021-02-08 2021-05-11 杭州临安科达环境科技研究所 一种梳型聚氨酯超分散剂的制备方法、分散剂及其应用
CN113201233B (zh) * 2021-04-29 2022-07-01 宁波中苑颜料有限公司 一种光致变色有机颜料及其制备方法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4915860A (en) 1987-01-09 1990-04-10 Nippon Oil Co., Ltd. Urea-urethane grease composition
US5852123A (en) 1996-10-17 1998-12-22 E. I. Du Pont De Nemours And Company Graft copolymer with a urea or imid functional group as a pigment dispersant
WO2004104064A2 (en) 2003-05-15 2004-12-02 The Lubrizol Corporation Polyurethane dispersants
US20100227950A1 (en) 2004-05-13 2010-09-09 Huntsman Petrochemical Corporation Comb-like polyetheralkanolamines in inks and coatings
US20110166316A1 (en) 2008-09-18 2011-07-07 Basf Se Polyurethanes based on polyester diols with improved crystallization behavior
US20140199524A1 (en) 2004-09-01 2014-07-17 Ppg Industries Ohio, Inc. Polyurethanes, Articles and Coatings Prepared Therefrom and Methods of Making the Same

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE654667A (ja) * 1963-10-22
US9598527B2 (en) 2004-09-01 2017-03-21 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
DE102007038041A1 (de) 2007-08-10 2009-02-12 Kronotec Ag Verfahren zur Vermeidung der Emission von Aldehyden und flüchtigen organischen Verbindungen aus Holzwerkstoffen
EP2970554B1 (en) * 2013-03-14 2023-09-20 PPG Industries Ohio Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4915860A (en) 1987-01-09 1990-04-10 Nippon Oil Co., Ltd. Urea-urethane grease composition
US5852123A (en) 1996-10-17 1998-12-22 E. I. Du Pont De Nemours And Company Graft copolymer with a urea or imid functional group as a pigment dispersant
WO2004104064A2 (en) 2003-05-15 2004-12-02 The Lubrizol Corporation Polyurethane dispersants
US20080167423A1 (en) 2003-05-15 2008-07-10 Stuart Nicholas Richards Polyurethane Dispersants
US20100216932A1 (en) 2003-05-15 2010-08-26 The Lubrizol Corporation Polyurethane Dispersants
US20100227950A1 (en) 2004-05-13 2010-09-09 Huntsman Petrochemical Corporation Comb-like polyetheralkanolamines in inks and coatings
US20140199524A1 (en) 2004-09-01 2014-07-17 Ppg Industries Ohio, Inc. Polyurethanes, Articles and Coatings Prepared Therefrom and Methods of Making the Same
US20110166316A1 (en) 2008-09-18 2011-07-07 Basf Se Polyurethanes based on polyester diols with improved crystallization behavior

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Kupryushkin, MS et al. "Efficient Functionalization of Oligonucleotides by New Achiral Nonnucleosidic Monomers" Organic Letters, vol. 16, May 12, 2014, pp. 2842-2845; p. 2842, scheme 1.

Also Published As

Publication number Publication date
MX391841B (es) 2025-03-21
US20170240756A1 (en) 2017-08-24
EP3218423A4 (en) 2018-06-20
MX2017006176A (es) 2017-07-31
KR20170083603A (ko) 2017-07-18
CN107075106B (zh) 2020-01-21
BR112017008202B1 (pt) 2021-11-03
WO2016077147A1 (en) 2016-05-19
BR112017008202A2 (pt) 2017-12-26
CN107075106A (zh) 2017-08-18
JP2018504259A (ja) 2018-02-15
JP6603714B2 (ja) 2019-11-06
EP3218423A1 (en) 2017-09-20
KR102465005B1 (ko) 2022-11-09
EP3218423B1 (en) 2021-01-06

Similar Documents

Publication Publication Date Title
KR101526527B1 (ko) 습윤제 및 분산제의 제조 및 용도
JP5377833B2 (ja) 分散剤及び分散安定剤用としての付加化合物
CA2599578C (en) Comb-like polyetheralkanolamines in inks and coatings
US20100216943A1 (en) Hydrophilicized hyperbranched polyurethanes
JP6566588B2 (ja) ポリアミン付加化合物
US10301489B2 (en) Comb polyurethane dispersants
EP2069434B1 (en) Comb-like polyetheralkanolamines in inks and coatings
EP2281012B1 (en) Dispersants from linear polyurethanes
US11879032B2 (en) Reaction products containing urethane groups and urea groups
CN107667130B (zh) 含有氨基甲酸乙酯基团的反应产物
US20050172853A1 (en) Recording liquids containing polyurethanes with hyperbranched structures
US9238766B2 (en) Comb-like polyetheralkanolamines in inks and coatings
Ahmed et al. Polyurethane prepolymers: an efficient dispersant core for sublimation inkjet inks
US10717875B2 (en) Comb-like polyetheralkanolamines in inks and coatings
CN111040181A (zh) 一种聚丙烯酸酯分散剂及其制备方法
CN113227282A (zh) 用于非水性涂料的粉末状触变剂及添加该触变剂的非水性涂料组合物
CN111065667B (zh) 多组分分散剂
EP4200347A1 (en) Urea urethane compounds

Legal Events

Date Code Title Description
AS Assignment

Owner name: HUNTSMAN PETROCHEMICAL LLC, TEXAS

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:KLEIN, HOWARD P;BERTENS, FRANK;VANDERSTRAETEN, PETRA;AND OTHERS;SIGNING DATES FROM 20160126 TO 20160201;REEL/FRAME:041979/0481

STPP Information on status: patent application and granting procedure in general

Free format text: NOTICE OF ALLOWANCE MAILED -- APPLICATION RECEIVED IN OFFICE OF PUBLICATIONS

STPP Information on status: patent application and granting procedure in general

Free format text: PUBLICATIONS -- ISSUE FEE PAYMENT VERIFIED

STCF Information on status: patent grant

Free format text: PATENTED CASE

MAFP Maintenance fee payment

Free format text: PAYMENT OF MAINTENANCE FEE, 4TH YEAR, LARGE ENTITY (ORIGINAL EVENT CODE: M1551); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

Year of fee payment: 4